Harpoon Oktoberfest in Boston - September 29-30, 2023 at Harpoon Brewery in Boston, MA! Click here for more info & tickets

Fairs & Festivals brighten the Berkshires every season of the year

In a landscape like this with so much natural beauty, history, creative and performing artists, craftsmen, food purveyors, wine and beer makers, there are lots of reasons and occasions to hold celebrations of every kind. Year-round this part of Massachusetts is filled with fairs, festivals and other events highlighting the richness found here. Each fall brings with it a special blend of activities for the whole family, as do the holidays and warmer months. Come for a family getaway to this sweet spot in New England and be delighted.
Oktoberfest 2023 at Wachusett

Wachusett Mountain Ski Area, 499 Mountain Road Princeton, MA Phone: 978-464-2300

September 30-October 1, 2023

Enjoy German food, music, traditional dancing, beer, craft vendors, a farmers' market, live shows, contests and more. Live music by the Hofbräu Spieler Band; stein hoisting contest, keg tossing contest, an inflatable obstacle course, and even a magic show!

Time: 11 a.m.-5 p.m.
Admission:$6-$9. Fee for Skyride is extra. See website